An Orlando native, Siler attended the University of Florida for college and quickly flourished as a team leader. He was named the SEC Player of the Year his freshman year and was a captain of the 2006 National Championship-winning team. Today, many of his former UF teammates still attribute their iconic success to Siler’s leadership; he knew how to relate to people and how to pull the best out of them, both on and off the field.
After his third year in college, he was drafted in the seventh round by the San Diego Chargers. After getting drafted lower than expected, Siler spent his four years in San Diego constantly having to prove his worth on the field. The 2011 NFL Lockout rerouted Siler’s time in the League, and he ended up playing for the Kansas City Chiefs.
His final year in the League was marked by tragedy and tremendous loss when his closest friend on the team passed away from suicide. The extreme heartbreak Siler experienced from the loss of his friend made him reevaluate what he wanted to do with his life. “I was done,” he said, “I just walked away after that year, knowing that I needed to do something else— I lost my love for the game.”